9-day Cleveland Way itinerary

1. Day 1

   Helmsley to Kilburn

   3–4 h 8.4 mi (13.6 km) ↑ 360 m (1,200 ft) ↓ 140 m (450 ft)

   A gentle start, with Rievaulx Abbey a short detour from the woods of Nettledale. The climb to Sutton Bank is steady, and James Herriot called the view over the Vale of York the finest in England. Kilburn is down off the edge below the White Horse, which keeps the first day short and puts a climb at the start of the second.

   Example stay The Forresters Arms

2. Day 2

   Kilburn to Osmotherley

   5–6 h 12.8 mi (20.7 km) ↑ 320 m (1,050 ft) ↓ 430 m (1,400 ft)

   Back up to Sutton Bank, then north along the limestone edge of the Hambleton Hills. Gormire Lake below is one of only three natural lakes in Yorkshire. The drove road is broad and easy but open to the weather, and there is nowhere to buy food, so carry lunch. Osmotherley has pubs and a hostel, and the hills start tomorrow.

   Example stay Vane House Bed and Breakfast Osmotherley

3. Day 3

   Osmotherley to Clay Bank Top

   5–6 h 10.9 mi (17.6 km) ↑ 840 m (2,750 ft) ↓ 710 m (2,350 ft)

   The hardest walking of the trip, which is why the day is short. The flags help, but the moor between them can be boggy after rain, and each climb is followed by a drop and another climb. Lord Stones café at Carlton Bank is the only stop. There is no bed at Clay Bank Top itself, so the night is at Clay Bank Huts, a short walk away, and they offer a pick-up.

   Example stay Clay Bank Huts (opens in a new tab)

4. Day 4

   Clay Bank Top to Newton under Roseberry

   6–7 h 13.8 mi (22.1 km) ↑ 570 m (1,850 ft) ↓ 550 m (1,800 ft)

   Longer than it looks, because both nights sit a short way off the path. Urra Moor is the high point, and in mist it is easy to follow a bridleway that leaves the Way, so check the line out of Clay Bank Top. Kildale is the first place to eat. From Captain Cook's Monument you drop off the ridge to the King's Head at Newton under Roseberry.

   Example stay The King's Head Inn (opens in a new tab)

5. Day 5

   Newton under Roseberry to Saltburn-by-the-Sea

   4–5 h 10.7 mi (17.2 km) ↑ 360 m (1,200 ft) ↓ 640 m (2,100 ft)

   The moors end today. Roseberry Topping is a steep spur with a wide view, worth the extra climb. Guisborough Woods follow, the longest forestry on the Way, where the junctions need watching. Farmland brings you down to Saltburn, its pier and Cliff Lift, for an easy evening before the cliffs.

   Example stay Saltburn House (opens in a new tab)

6. Day 6

   Saltburn-by-the-Sea to Runswick Bay

   5–6 h 12.6 mi (20.3 km) ↑ 490 m (1,600 ft) ↓ 520 m (1,700 ft)

   The first day on the cliffs, short in miles and steep in places. The drop into Skinningrove and the climb to Boulby, the highest cliff on England's east coast, come early, and the edge is unfenced in places. Staithes, an old fishing village with pubs and cafés, is the stop for lunch. Runswick Bay is a short walk beyond.

   Example stay The Royal Hotel (opens in a new tab)

7. Day 7

   Runswick Bay to Robin Hood's Bay

   6–7 h 15.2 mi (24.5 km) ↑ 500 m (1,650 ft) ↓ 460 m (1,500 ft)

   Drops into bays and climbs back out, from Runswick Bay to Sandsend. Whitby breaks up the day, and it is where to buy supplies, because Robin Hood's Bay has no large shop. After the abbey the cliff top is easy going, and Robin Hood's Bay waits at the end, its houses packed onto the cliff edge.

   Example stay North Ings - Robin Hood's Bay (opens in a new tab)

8. Day 8 Longest

   Robin Hood's Bay to Scarborough

   7–8 h 15.7 mi (25.3 km) ↑ 560 m (1,850 ft) ↓ 600 m (1,950 ft)

   The longest day of the plan, and the hilliest on the coast. The path drops to sea level at Boggle Hole and again at Stoupe Beck, then climbs gradually to Ravenscar. Later, Hayburn Wyke's wooden steps are slippery after rain. Keep something in reserve, because these small climbs tire you late in the day before Scarborough.

   Example stay Clifton Hotel Scarborough (opens in a new tab)

9. Day 9

   Scarborough to Filey

   3–4 h 8.1 mi (13.1 km) ↑ 250 m (800 ft) ↓ 210 m (700 ft)

   The easiest day on the coast, and a gentle finish. The cliffs run above Cayton Bay and past Holbeck, where a hotel slid into the sea in 1994. Filey Brigg, a rocky point out into the sea, is the end of the trail. Take care on its rocks when they are wet, and leave time for the train home from Filey.

   Finish Cleveland Way Finish

Cross-check: Cleveland Way trail information on National Trails . The trail body lists 9 days for the 109 miles (175 km). Distances on the cards are measured along the trail on our line. A walk off the path to a bed is extra.

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